


Obsession

by thewinchesterlifestyle



Category: Supernatural
Genre: Bondage, Bottom Dean, Cas/OMC(s), Chains, Cock & Ball Torture, Cock Cages, Dildos, Doctor Castiel, Exhibitionism, Fucking Machines, Gags, Hurt Dean Winchester, Kidnapping, Killer Castiel, M/M, Multi, Murder, Obsessive Castiel, Orgasm Delay/Denial, Physical Torture, Psychological Torture, Restraints, Rough Sex, Sadist Castiel, Serial Killer Castiel, Sexual Torture, Size Kink, Small Penis, Sounding, Stalker Castiel, Stalking, Top Castiel, Torture, Victim Dean, Violent Sex, Whipping, forced voyeruism, mentioned dean/omc(s), victim omc, violent castiel
Language: English
Status: Completed
Published: 2016-12-16
Updated: 2016-12-16
Packaged: 2018-09-09 01:45:34
Rating: Not Rated
Warnings: Rape/Non-Con
Chapters: 1
Words: 3,222
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8870938
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: Castiel had spent weeks watching Dean Winchester. Weeks of learning his schedule, his patterns and slowly becoming more obsessed. His victims hadn’t been able to truly catch his attention since he'd first seen Dean and Castiel  had been forced to imagine Dean in their place in order to experience the usual pleasure he typically enjoyed.





	

**Author's Note:**

> READ THE TAGS!!!
> 
> This was written for two prompts.

Castiel had spent weeks watching Dean Winchester. Weeks of learning his schedule, his patterns and slowly becoming more obsessed. His victims hadn’t been able to truly catch his attention since he’d first seen Dean and Castiel had been forced to imagine Dean in their place in order to experience the usual pleasure he typically enjoyed.

He released a soft sigh before slipping inside Dean’s home and moving silently through the house. Castiel knew where to avoid creaky floors and various objects, having been inside the house several times, as he walked towards the bedroom.

On the bed lay Dean, sprawled out in nothing but a pair of boxers, as he breathed evenly. It was perfect. Castiel stepped closer to the bed and watched as Dean’s eyes shot open at the creak of the floorboard. The younger guy jerked and started to shoot up in bed but Castiel had more than enough experience subduing his victims. He easily covered Dean’s mouth and nose with the drug soaked rag.

Dean’s movements slowed and then he slumped against the sheets unconscious.

Castiel cocked his head to the side and allowed himself to enjoy the sight before he hefted Dean up from the bed.

It took a little to get him into his trunk but once Castiel had shut it he couldn’t keep the pleased expression off his face.  _Now_  he could enjoy that delicious body he’d been imagining. He could spend hours and days…possibly  _weeks_  with Dean before the fun ended as it always did.

He was careful as he parked his car in his garage, careful as he carried Dean down into his soundproof basement where he set up his equipment for each of his  _sessions_.

Castiel looked around trying to decide where he wanted Dean first before electing to chain him up. He secured chains around each of Dean’s wrists and another set that were attached to the floor to his ankles. “Beautiful.” The word was breathed out as he looked at the metal against Dean’s skin.

A frown stole over his features at the sight of Dean’s boxers. Castiel went over to where he kept his special tools and grabbed a knife to cut Dean’s boxers from his body until the gorgeous guy was completely naked.

He reached out and ran his fingers over Dean’s small soft cock, trailing down to touch his captive’s balls and then back up to map Dean’s bare body with the tips of his fingers. Dean was gloriously hairless between his legs and it didn’t surprise Castiel

Observing Dean had taught him Dean was one of the biggest bottom bitches he’d ever seen and it had been more than obvious what a slut Dean was for a good, hard fucking. The small cock could only belong to a pretty, greedy bottom.

Possibilities ran quickly through his mind before he decided to simply make use of Dean’s holes. It wasn’t as though Dean didn’t enjoy having something filling him at either end. The serial killer moved back over to where he kept some of his favorite toys and brought them over.

The first one he selected was a cockcage with a sound. He focused on the task before locking it and turning towards the table for the next item.

Castiel settled on a large ball gag and quickly pressed it inside Dean’s slack mouth, securing it behind his victim’s head, before he stepped back to admire the image. Dean was hanging from the ceiling from his chains with lips stretched around a bright red ball-gag and his small cock carefully caged. He stood there for a moment and grabbed up a black blindfold so he could cover Dean’s closed eyes.

He finally tore his gaze from Dean and back to the different toys laid out. There were vibrators and dildos of varying sizes, he preferred the large sex toys for his current projects, as well as vibrating dildos. Briefly he thought about the anal beads and some of the more intriguing toys but finally he settled on one of the largest vibrating dildos. Dean’s hole needed to be stuffed full and the sight of it against Dean’s flat belly would be glorious.

It would be nothing but the best for his pretty obsession.

Castiel grabbed the bottle of lube and stared. It would be easier if Dean wasn’t hanging for the next part. He stepped up and slowly lowered the chains until Dean was touching the floor. After some maneuvering he started to open Dean up.

He had to be careful at this stage, not wanting to ruin his new  _toy_  so soon, as he pumped lube slick fingers inside Dean’s hole. The feeling of tight heat around his fingers had his cock filling with interest and Castiel allowed himself a groan of pleasure.

It was only the knowledge that he could have as much time as he wanted with Dean’s body that allowed him to wrestle control back instead of fucking right into Dean. Two fingers became three as he pressed against Dean’s insides until he felt Dean adjusting and then he worked a fourth inside.

The toy he’d chosen was large enough to rate four fingers for prep if he didn’t want to tear anything. Honestly four fingers might not be enough but he hadn’t gotten the truly monstrous dildo out.

_Yet._

A soft moan escaped Dean’s lips as the muscles under his skin twitched and he shifted from his place on the hard floor. Castiel withdrew his fingers and reached up to grab the large toy. He coated the shaft with more lube and pressed the head against Dean’s loose hole.

The tip popped inside as Castiel pushed it all the way in. It took some adjust, even more lube, and persistence to work it completely inside. There were soft sounds of discomfort, some of pain, and Dean shifted as Castiel worked but Dean’s eyes remained closed for the time being. Castiel allowed himself to admire the stretch of Dean’s rim around the toy. His fingers held Dean’s cheeks open before he released Dean to start lazily pumping the toy into Dean.

His imagination quickly replaced the fake cock with his own and the press of his cock against his pants had another groan escaping him. Without a second thought he turned the dildo on and angling it he found Dean’s prostate.

The chains rattled and Dean’s whole body jerked as he moaned. Castiel was sure Dean’s eyes were wide open behind the blindfold as his captive frantically moved his head around. “There we are.” He purred the words and grinned when Dean suddenly froze. “I’m going to have so much fun with you.”

Dean tried to talk but the words were muffled by the ball-gag. He jerked and squirmed but Castiel didn’t pause in his motions until Dean was writhing before him on the floor. He kept the vibrating dildo against Dean’s prostate and turned it to the highest settling.

There were more moans and the chains rattled against the floor as Dean tried to both squirm away and press into it in hopes of more pleasure. “Look at your ass stretched around my dildo.” Castiel thrust it inside a few more times before pulling it out and watching Dean’s hole clenching around nothing.

Suddenly Dean moved to grab his blindfold and Castiel released a displeased sound as he quickly moved to yank the chains. Dean’s arms were jerked up and he flailed as he was hoisted back up so his arms were raised high above his head.

“I’m afraid the blindfold stays on or you can opt to have those pretty green eyes of yours blinded. Your choice. Though I would _love_ to have them in a glass jar on my shelf.” He watched Dean’s struggling pause and a few seconds later Dean was sagging in his chains. More muffled words escaped but Castiel didn’t care about them.

What he cared about was pressing  _his_  cock inside that pert ass and fucking to the sound of Dean’s subdued moans and the sounds of rattling chains. He lowered the chains slightly so Dean had a little give and quickly secured them.

He wasn’t denying himself any longer.

Castiel could enjoy Dean’s body and use every single one of his instruments over the course of Dean’s captivity. He freed his aching cock and pressed a hand between Dean’s shoulders to guide him forward. “Good boy.” He grinned around the words while pulling his hand back and guiding his cock inside.

Dean released another muffled sound and jerked in his chains but Castiel gripped Dean’s hips and slammed himself inside with a pleased groan.

The chains rattled violently and Dean’s ass clenched around him, tight and hot, as Castiel drew back and started up a brutal rhythm. He let himself enjoy the pleasure slowly building inside and the way Dean’s hole was tightening around him.

He couldn’t remember a victim of his that had felt this good and it was only the first day with him. “Should have taken you sooner instead of that mouthy red head.” Castiel let his eyes slide closed as he gave over to the carnal act. “He wasn’t a bad fuck but you’re better. Maybe it is the anticipation that’s built up since I first saw you.”

Dean was tugging at his chains and his legs were shaking but Castiel didn’t care about those things. He kept moving quicker and quicker until his thrusts fell off their rhythm. His breathing picked up as he moaned and his cheeks flushed with pleasure.

“I’m usually far rougher but I want you to last. We’ll save the more…violent methods for when we’re closer to the end.”

The pleasure he had struggled to find with his other victims after first seeing the beautiful green eyed guy he was currently fucking surged inside of him.

When Castiel came he slammed viciously inside Dean and moaned low in his throat while his cock shot his load into Dean’s clenching hole. “Fuck.” He breathed and pressed his forehead against Dean’s warm back. “I’m keeping you longer than the others.” Castiel could always sate his need to spill blood and hear his victims sobbing, begging for their lives, with others while he kept Dean chained.

The serial killer pulled away and watched his cock slide free of Dean’s hole. He blinked at the thought of Dean chained up and watching him with another victim. He wondered about Dean’s various expressions as he fucked and tortured and killed someone else. It was enough to have his cock give a twitch of interest but it was too soon to get hard again.

Dean swayed in the chains and more mumbled sounds filled the room. Castiel stared at his come leaking from Dean’s abused hole and looked back over at his toys. He started to decide what he wanted to do with Dean’s pretty body next.

There were so many wonderful options.

* * *

Castiel whistled as he moved around Dean’s unconscious body, preparing him for the evening. Dean’s head was secured so he was facing forward toward where Castiel had his newest victim chained. Next he carefully used the eye speculums so Dean’s eyes would remain open. When he finished a ball-gag was secured in Dean’s mouth before he checked the bands he’d used to pin Dean’s arms to his sides.

“You always look so perfect tied up.” His hand stroked down Dean’s back and over the swell of Dean’s ass. Castiel forced himself away from admiring Dean’s bare body so he could hook Dean to the table. He checked where Dean’s legs were held apart by a spreader bar and nodded in satisfaction.

There was a groan across the room that had him looking up to meet wide, terrified brown eyes that were darting around the room before settling on him.

“Don’t worry. Once I set up the fucking machine I’ll be giving you all of my attention.” His eyes tracked over the other’s naked body with interest.

The guy wasn’t as pretty as Dean but after thorough research and observations he was looking forward to playing with his new victim. He was looking forward to fucking into a new body and feeling the warmth of the guy’s blood when he was finished.

Castiel grinned when he heard muffled begging. He had been hard since he’d acquired Thomas but the sounds Thomas was making had him aching. “I might start off fucking you.” Chains rattled and the muffled sounds pitched higher in desperation.

He returned his focus to Dean, checking his hole to make sure it was slick and loose enough, so he could guide the head of the dildo inside. Dean released a low groan and twitched on the table when Castiel bottomed the toy out. He admired it stretching Dean open, stepping back and turning the fucking machine on.

There was a low hum in the room as it pumped in and out of Dean at a quick pace.

Castiel watched it before turning all of his attention to the man struggling on the floor. “Hello, Thomas.” He stepped closer and grabbed a few of his toys. “I know we saw each other only yesterday for your physical but I hope you won’t mind me taking a more personal look.”

He let his eyes linger on the chains holding Thomas down.

Castiel reached for the chain and hoisted Thomas up so he was dangling from his arms, pained sounds muffled by his gag, as he twisted. There was a louder moan behind him and Castiel grinned at Thomas. “Sounds like Dean is awake and just in time.”

There were more muffled groans from Dean but Castiel didn’t look behind him. He turned to his tools and selected the cat o’nine tails. Thomas stared at it and struggle harder but the sight only had Castiel’s arousal increasing.

He  _loved_  when his victims struggled.

The first strike across Thomas had a muffled howl escaping. Castiel paused to relish the sound. His fingers tightened around it before he started bringing it down hard against Thomas. It whipped through the air and stuck Thomas again and again until he was hanging there limply, tears rolling down his cheeks and chest heaving.

“I’m sure by now you can’t help but feel arousal.” Castiel spoke to Dean as he dragged his fingers through the wounds he’d inflicted on Thomas. Blood came away and he wiped it on Thomas’s tear stained cheeks. “Only way you’re coming is coming untouched while you watch me with Thomas.”

Dean released another sound but Castiel was already turning his attention on his next toy. He unhooked Thomas who slumped against him, moaning brokenly, so he could move closer to the wall.

“This is one of my favorite ways to fuck Dean.” Now he glanced back at Dean to see those wide green eyes staring at him in horror. “I’m sure you’ll enjoy it too.”

He set about stretching Thomas’s arms high above his head, fixed to the wall, before taking the chain hooked around his left ankle to pull up and secure to the metal links on the wall. He repeated the action with the right ankle so that when he was finished both of Thomas’s legs were lifted high and spread open to expose him for Castiel.

“Sometimes I leave Dean in this position and come down to fuck him throughout the day. He’s got such a greedy hole that when I’m not fucking him I’m always sure to have a toy stuffed inside.” He reached out to stroke Thomas’s soft cock. It earned a groan that changed to a high yelp and a violent jerk when he pinched the skin of Thomas’s balls, twisting, while staring at Thomas’s pain filled eyes.

Castiel moved back to his tools. He used a larger dildo, slicking it up, to press against Thomas’s hole. He started pushing it inside ignoring the violent thrashing and muffled screams. There was the usual resistance but it didn’t stop him as he stared into agony filled brown eyes.

“I use more care with you, Dean, since my current intentions are to keep you longer. At least for now.” He pushed the toy in further and started fucking Thomas with it. The screams and howls increased but he knew they’d be piercing if the gag was gone. The position and the size of the toy shoving deep had to be agonizing. “I’ve told you before, though, that toward the end of our relationship things will get much…rougher when the need for care fades.”

Once Thomas went limp again, bleeding and crying silently, Castiel set his toy down and set about removing his clothing. He collected his lube and slicked himself up before moving closer.

“Don’t worry. I am very thorough in making sure none of my play things have any diseases. I do prefer to fuck with nothing between us.” He guided his cock forward and sank into Thomas’s abused body with a pleased moan. Thomas weakly twitched and moaned into his gag. Castiel could feel Thomas’s abused hole clenching around him as he started fucking inside the guy’s ass with enthusiasm.

He knew Dean had a view of his bare body fucking into another guy. The sound of Dean being fucked by the machine and Thomas’s broken moans had him slamming inside harder, chasing his orgasm. His body felt on fire and pressure building inside him raced through his body.

Castiel feel that dark place inside him urging him quicker and harder until he slammed inside the limp body to come with a groan. He rested his face against Thomas and slowly started to steady his breathing.

He pulled out and took in the sight of Thomas’s abused body. There were marks from where he’d whipped him and it was more than obvious he’d done damage with the dildo. Castiel turned away to leave him hanging there and walked over to Dean, stroked his cheek with a bloody hand. “Don’t worry, Dean. You’re still the best I’ve had.”

Days later, after Castiel had visited multiple forms of torture that had Thomas howling and violently shaking, there was a dead body on his basement floor. Blood and come covered Thomas where Castiel had left him.

He left Thomas there and turned back to look at Dean with wild eyes. Every single inch of him felt hyperaware and his excitement was impossible to contain. He’d missed watching the life leave someone’s eyes and the sight of someone dying under him. “We’ll have to do this again. Soon.” Dean was crying on the table and the muscles in his body were twitching from too much overstimulation. He’d spent days, with only the shortest of breaks, getting fucked by increasingly larger dildos while Castiel played. “I have a list. We’ll see what I pick for next time.”

It had only been two weeks since he’d brought Dean down here and there were still so many things Castiel was very interested in doing before he finished. Dean Winchester would be his masterpiece and Castiel didn’t mind dragging it out longer.

After all once he was finished with Dean he couldn’t simply start over. He would have to move on to his next obsession but for now he could focus on Dean and store away their time for later reflection.


End file.
